Colupulone

Details

• Internal ID: d4c627e3-d2ee-41b0-a7ea-aec907ba4561
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
• InChI: InChI=1S/C25H36O4/c1-15(2)9-10-19-22(27)20(21(26)18(7)8)24(29)25(23(19)28,13-11-16(3)4)14-12-17(5)6/h9,11-12,18,27-28H,10,13-14H2,1-8H3
• InChI Key: UNCDMWKTFLUPHZ-UHFFFAOYSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.26135963 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.47
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• 468-27-9
• BA8R555DNZ
• NSC650561
• UNII-BA8R555DNZ
• 3,5-dihydroxy-2-isobutyryl-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
• 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(2-methyl-1-oxopropyl)-
• Colupulone A
• Colupulone I
• I-BUTYROLUPUPHENONE
• SCHEMBL316240
• DTXSID80963664
• CHEBI:136851
• HY-N10867
• NSC-650561
• 21621-94-3
• XC172848
• CS-0637301
• Q27458763
• 3,5-dihydroxy-2-isobutyryl-4,6,6-tris(3-methyl-but-2-enyl)cyclohexa-2,4- dienone
• 3,5-Dihydroxy-4-isobutyryl-2,6,6-tris-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienone
• 2,4-CYCLOHEXADIEN-1-ONE, 3,5-DIHYDROXY-4,6,6-TRIS(3-METHYL-2-BUTEN-1-YL)-2-(2-METHYL-1-OXOPROPYL)-
• 3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• 3,5-Dihydroxy-4,4,6-tris(3-methyl-2-butenyl)-2-(2-methylpropanoyl)-2,5-cyclohexadien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9799	97.99%
Caco-2	+	0.6940	69.40%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8296	82.96%
OATP2B1 inhibitior	-	0.7104	71.04%
OATP1B1 inhibitior	+	0.8582	85.82%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4498	44.98%
P-glycoprotein inhibitior	-	0.7176	71.76%
P-glycoprotein substrate	-	0.7724	77.24%
CYP3A4 substrate	-	0.5105	51.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.9219	92.19%
CYP2C9 inhibition	-	0.6567	65.67%
CYP2C19 inhibition	-	0.7102	71.02%
CYP2D6 inhibition	-	0.8982	89.82%
CYP1A2 inhibition	-	0.9000	90.00%
CYP2C8 inhibition	-	0.9560	95.60%
CYP inhibitory promiscuity	-	0.8153	81.53%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7876	78.76%
Carcinogenicity (trinary)	Non-required	0.7054	70.54%
Eye corrosion	-	0.9636	96.36%
Eye irritation	-	0.4804	48.04%
Skin irritation	-	0.5603	56.03%
Skin corrosion	-	0.9209	92.09%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6446	64.46%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6429	64.29%
skin sensitisation	+	0.6084	60.84%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.7464	74.64%
Acute Oral Toxicity (c)	II	0.4861	48.61%
Estrogen receptor binding	+	0.7829	78.29%
Androgen receptor binding	+	0.5406	54.06%
Thyroid receptor binding	+	0.5540	55.40%
Glucocorticoid receptor binding	+	0.7665	76.65%
Aromatase binding	+	0.5449	54.49%
PPAR gamma	+	0.8701	87.01%
Honey bee toxicity	-	0.8641	86.41%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.66%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.24%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.19%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.58%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.10%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.05%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	83.54%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.49%	90.71%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 373677
• NPASS: NPC126224
• LOTUS: LTS0082637
• wikiData: Q27458763